


Issei's Lusty Introduction to Life as a Devil

by hugplx



Category: Highschool DxD (Anime)
Genre: Cuckolding, F/M, Promiscuity, Sadism, Teasing, Vanilla
Language: English
Status: Completed
Published: 2021-01-31
Updated: 2021-01-31
Packaged: 2021-03-17 18:42:23
Rating: Explicit
Warnings: No Archive Warnings Apply
Chapters: 2
Words: 7,772
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/29105025
Author URL: https://archiveofourown.org/users/hugplx/pseuds/hugplx
Summary: Throwing boulders and being able to do magic is all well and good, but Issei didn't really see what was so great about being a devil until he truly got to know the two Great Ladies of Kuoh Academy.Snippets of Issei's erotic adventures as a devil. OOC Issei.
Relationships: Hyoudou Issei/Multi
Comments: 14
Kudos: 11





	1. Chapter 1

**Chapter 1: Gaming the System**

  
  


This whole ‘Devil’ thing was weird and confusing, Issei mused with a skip to his step. It wasn’t even the supernatural craziness that baffled him - a life of consuming anime and video games had prepared him rather well on that front, unsurprisingly.

  
  


No, it was the more mundane aspects of devlish life that he found strange. Advancement, for one.

  
  


He’d been promised his heart’s desires from his king when he’d been recruited into her peerage. All he had to do was grow in strength and advance as a devil and not only could he get his own Evil Pieces in time, but his own noble title and lands too. Anything, really.

  
  


So, how did one grow in strength and advance?

  
  


It wasn’t by drinking juice, lifting weights and running five kilometers a day like he’d thought, no. It was with  _ contracts _ .

  
  


As a devil, his body was more physically powerful and even had the ability to do  _ magic _ , but that was limited by his demonic power.  _ Power _ limited the strength of his magic,  _ power _ limited how much of it he could pump through his body and boost his strength and speed, and  _ power _ limited how much of it he could use before his body became fatigued.

  
  


In days of old, devils used to rip the souls out of humans and consume them to replenish and boost their power. Thankfully - according to Rias - that practise was outlawed generations ago. Now, devils had contracts as a means to attain more power for themselves, and their kings.

  
  


While consuming souls was outlawed, devils still gained power through their contracted humans’ essence, they just didn’t drain them dry anymore, as it were. Rias had explained it to him rather simply. Devils feed off the desires of humanity, the stronger the desire, the stronger the power they siphon from it. She’d summed it up by calling them ‘emotion vampires,’ and Issei instantly understood.

  
  


He’d blushed up a storm when Himejima Akeno, his new insanely beautiful senpai, had whispered into his ear in the midst of his education that she liked to siphon power off her contracted humans’ lustful desires.

  
  


With an insanely erotic body lilke hers, Issei wasn’t surprised when she revealed how powerful she truly was.

  
  


Which made the  _ look _ she gave him when he summed up her method as prostitution that extra bit more terrifying,

  
  


Rias had found their exchange highly amusing, the best friends often keen to tease one another or see them be teased.

  
  


‘Be that as it may,’ Rias had headed off her friend before she could fry her new Pawn, ‘Akeno’s method is highly effective and has made her one of the most powerful devils of our generation. You should learn from your senpai.’

  
  


‘Pfft,’ Issei had scoffed and waved her off. ‘I could easily get more than the hooker, just you watch!’

  
  


Rias had to step in at that point before Akeno electrocuted her new pawn.

  
  


‘Big words, Issei-kun. How about a wager then? To see who can harvest the most power from their contracted humans?’ Rias had tempted him with her beautiful teasing smile, her cheek resting against her fist and her pale legs crossed, revealing a sinful amount of upper thigh with her ridiculously short skirt.

  
  


Issei wasn’t too proud to admit he’d gulped at the suggestive tone and the way lightning had crackled between the madly grinning Akeno’s fingers.

  
  


‘What are the stakes?’

  
  


‘If you fail to harvest more power than Akeno in one evening, you’ll have to  _ entertain _ her for one whole night.’

  
  


Had that sentence been uttered to him before he’d met and gotten to know his beautiful senpai, Issei would have thrown the contest right there. The way her breath quickened and lightning continued to dance along her delicate fingers however, he doubted he’d find the evening very  _ entertaining. _

  
  


‘And when I win?’ he had asked with a confidence he had only marginally felt in that moment.

  
  


‘I assume you’re still a virgin?’ Rias asked with a teasing smile.

  
  


Issei had bristled and blushed at the question. ‘It’s perfectly normal to still be a virgin at seventeen!’ 

  
  


Once Rias and Akeno had stopped giggling at the embarrassed teen she continued. 

  
  


‘Well, if you win, maybe you can see your first real-life  _ pussy _ ?’ 

  
  


Issei had agreed so fast he had made Rias’ head spin. He didn’t even care to ask for specifics. Would he get to fuck Akeno? Rias?  _ Both?! _ He didn’t care.

  
  


He had developed a genius plan to beat Akeno and he was confident of his victory. While Issei knew more than anyone how great a motivator sex was, it was nothing compared to  _ hunger _ . 

  
  


With his parents living overseas for work, he had become a pretty excellent cook to help save money - mainly so he could pocket the food allowance his parents sent him…

  
  


He had enlisted the help of his new peerage-mate Kiba - who also had a vested interest in seeing Akeno brought down a peg - to help hand out contracts to the needy. Homeless, impoverished, orphans - anyone who could use a hearty meal. He’d set up his stall on the street and was inundated with people handing in the signed contract for a beautifully cooked omurice.

  
  


He cooked for  _ hours _ , with several woks going at a time and a crowd gathered around to watch, he was certain he was going to earn his victory. With his impressive skill he had been able to feed everyone that came. He had  _ felt _ the power rolling in as he satiated these peoples’ hunger and entertained them with his cooking skill.

  
  


He didn’t finish until well into the evening, returning the cooking implements to the nearby restaurant he’d rented them from before rushing to the station to catch the last train home. Issei didn’t realize how exhausted he truly was until he sat down in the empty train compartment and rested his head against the window.

  
  


He was startled out of his past musings by his buzzing phone. Looking up with bleary eyes he let out a sigh of relief when he confirmed he hadn’t missed his stop while reflecting on the previous days’ events.

  
  


‘Yo,’ Issei answered the phone without looking.

  
  


_ ‘Congratulations my magnificent pawn,’ _ Rias’ sensual voice - even more sensual than usual, his bleary mind didn’t fail to notice - greeted him on the other end. 

  
  


‘Heh, was there ever any doubt?’ He replied cockily, wondering how she knew he’d won already and if she could feel the power flowing through her like he did. ‘I can’t wait to see the look on Akeno’s face.’

  
  


Rias’ giggle at that remark was interrupted by an erotic moan and Issei instantly perked up.

  
  


_ ‘Is she getting ready for me?! I’m not tired anymore!’ _

  
  


_ ‘She was quite...’ _ Rias paused as she moaned softly again,  _ ‘...put out.’ _

  
  


Issei was rock hard. He didn’t know if devils just naturally exuded sexual charm, but it felt like Rias could do that to him by just smiling in his direction.

  
  


_ ‘You’ll have to tell me what you did to win,’  _ she continued while breathing heavily. There was also a soft slapping sound he could barely make out in the background and he pervertedly wondered if she was slapping her own clit while masturbating. 

  
  


‘So…’ Issei broke the silence, his cheesy and awkward grin audible in his tone.

  
  


_ ‘I suppose you want your reward then?’  _ Rias replied with a delighted giggle. Issei’s face heated up and he replied in the affirmative.

  
  


_ ‘Enjoy, Issei-kun, you earned it.’  _ Rias cut the call then and Issei looked at his phone in confusion. She definitely had a cheeky tone to her voice just before hanging up, but Issei couldn’t puzzle the meaning. 

  
  


_ ‘Maybe she’ll let me fuck her another night?’  _ he naively thought as his phone buzzed again.

  
  


It was a picture message. Issei perked up and quickly opened the text from the prez. His goofy smile turned to one of bemusement when he saw the incredibly erotic pic.

  
  


The picture, enlarged to take up the entirety of his phone’s considerable screen, was one of an incredible pussy, just like Rias had promised. The skin was pale and the perfect pink lips unobscured by mosaics or any kind of censorship.

  
  


The pussy also had an incredibly thick cock in the process of fucking it, the pretty pink lips stretching obscenely around the dark and girthy member. The cock was so thick Issei mused it was probably a porno clip of a random girl fucking herself with a dildo.

  
  


_ ‘That thing has to be as thick as a can of Pringles…’ _

  
  


_ ‘ _ **_I thought you were going to let me fuck you_ ** **.** **_I didn’t think you’d cheap out on our bet and just send me a random porno pic from the internet.’_ **

  
  


Issei didn’t need to wait long for a reply to his text, though his leg bounced with frustration and impatience. He felt cheated.

  
  


**_‘Who said anything about fucking me? Our deal was you’d get to see a real-life pussy._ **

**_And who said I got this picture from the internet?’_ **

  
  


Issei frowned at the first part of the message and had to concede defeat. He’d let his excitement get the best of him, allowing the prez to manipulate him.

  
  


The second part of the message took a little more time to register in his exhausted mind, but when it did, it went off like a  _ bomb _ .

  
  


**‘** **_NO FUCKING WAY! THAT’S YOU?! Why do you even have dildos that big?! That’s so hot!’_ **

  
  


Issei waited for the reply from his incredibly beautiful and slutty senpai, his leg back to bouncing in anticipation. He opened the previous pic again and saw it in a whole new light. He wanted to blow up and frame this extreme close-up of Rias’ pussy and hang it on his wall, but failing that, it’ll go in his wank bank forever.

  
  


A reply wasn’t quick in coming, however, and when the train pulled up to his stop, he was forced to pocket his phone and disembark. Retrieving his bike from the bike lock he’d left it in, he rushed home, eager to find out if Rias thought her end of the deal was fulfilled, or if she’d be making further deposits in his wank bank.

  
  


* * *

  
  


Issei almost tore the door off its hinges in his rush to enter his empty house. He had two messages from Rias and he couldn’t wait to read them. 

  
  


He dropped into the plush couch in the living room and opened his messaging app. The first message was a simple text.

  
  


**_‘Oh my precious pawn,’_** it read, and Issei could practically feel the affectionate yet also patronizing tone she normally took with him, **_‘That’s adorable. I haven’t used a dildo in years. Why would I when I have easy access to fine specimens like Michael here?’_**

  
  


Issei’s eyes widened in shock when he scrolled down to see the picture she had sent. 

  
  


Rias was laying face down on what he presumed to be her bed while holding her phone out in front and above her to take a selfie. Her impishly grinning face was in the lower left of the frame while her voluptuous naked body filled most of the rest of it. This wasn’t a simple nude photo, though. What shocked him was the man she had captured in the selfie with her.

  
  


He had his pelvis pressed against her fleshy ass, clearly in the process of fucking her with one hand resting on her lower back while the other curlsed around underneath her, likely playing with her clit. All he’d seen of the guy he was incredibly jealous of was his milk-chocolate skin tone, his shredded physique and, from the first pic, his obscenely huge cock.

  
  


He was shocked out of reverie when he received another message. This one was taking a while to load and Issei felt his pulse quicken when he realized it was a video clip.

  
  


When it finally loaded, he hit play. Rias’s lover had clearly taken her phone at this point because the clip was from his point of view, and the whole picture swayed in time with his thrusts. It started with the lens aimed at the back of Rias’ head, buried in a pillow as she moaned in pleasure. Her curtain of crimson hair was pulled over her shoulder, allowing a view of her pale back as he traced the lens down her spine until it got to her glorious, pillowy ass and his huge cock thrusting in and out of her pussy. The obscene rod was a darker tone than his skin and it was slick with his king’s juices as it speared in and out of her.

  
  


He then flipped the camera around to show Issei his grinning face.  _ ‘Sorry man, your girl said her boyfriend got off on her fucking guys with big dicks. You don’t mind, do ya?’ _

  
  


‘ _ What?’ _ Issei thought in befuddlement. 

  
  


_ ‘I mean, I’m insanely jealous that he gets to fuck buchou instead of me, but she’s not my girlfriend…’  _ Issei thought in confusion before understanding dawned on him. 

  
  


It seemed Rias was as slutty as her best friend. It also seemed she had a wicked NTR kink that she was trying to roleplay. He felt no shame in whipping out his dick and beating off to the best ameteur porn he’d ever seen in his life. It was a far cry from getting to fuck her himself, but if Rias hoped he’d despair at the thought of other guys fucking her, she was barking up the wrong tree.

  
  


He had to wait twenty minutes until he got another message, but Issei was thrilled when he realized it was well worth the wait.

  
  


The clip was still from Michael’s point of view. He was on his back this time as Rias rode his huge cock while biting her lower lip lustily. She rode him hands free, one leg resting on her knee while the other had her foot planted on the bed so she could control the fucking. Her hair fell around her face like a curtain as she looked down on Michael lovingly while her hands fondled and played with her prodigious tits.

  
  


_ ‘You like riding that big dick baby?’  _ Issei heard Michael ask the smiling devil.

  
  


_ ‘Mhmm,’  _ Rias moaned in reply. ‘ _ You’re so much bigger than my boyfriend…’ _

  
  


Issei could only roll his eyes at the byplay, though if he were honest with himself, he  _ was _ a little jealous of that guy’s massive dick. How could he not be? His own was only slightly above average - he checked, with a ruler - but it was clear Rias liked them… big. Bigger-than-porn-star big at that…

  
  


Still, he tuned out their NTR play and just locked in on Rias’ tits - arguably her best feature- as she squeezed and played with them. He loved how her tit flesh escaped out from between her fingers when she squeezed tightly enough, he also loved how puffy and pink her large nipples were. If nothing else, he’d have to thank her for her heroic deposit into his wank bank.

  
  


It seemed Rias was too busy to send him any more pics of her evening, so after a truly epic wank session and a shower, he was just about to climb into bed when his phone pinged a couple more times.

  
  


**_‘I feel like I didn’t properly pay up on our bet. It’s not fair to you if there’s a massive dick in the way, right?’_ **

  
  


The text was followed by another video clip. When he hit play, the clip started with Rias holding the phone up to her face in selfie mode. She was grinning at him through the lens and blowing him a kiss. He noticed that her skin was covered in an alluring sheen of sweat that reflected the light and made her look even more sexy. Biting her lip, she let the camera trail down her shiny body, her massive tits hanging free and heavy on her chest. It then trailed over her flat tummy before stopping at her utterly soaked and thoroughly used looking pubic region. From the angle she held her phone, not only could he see her pussy in the most unobstructed way yet, he could also see her face still grinning down at him through the gap between her hanging tits.

  
  


Her delicate fingers ran up and down her drenched pussy lips several times before she spread them wide open, revealing to Issei her still slightly gaping entrance. Issei then groaned aloud when copious amounts of cum started leaking out of Rias’ abused pussy, accompanied by the sounds of her sultry giggles. 

  
  


He ignored the sound of Michael laughing in the background.

  
  


**_‘Did you enjoy the spoils of our bet, my beloved pawn?’_ **

  
  


After recovering from the insanely erotic sight he’d just seen, Issei made sure to save the most recent clip to his favourites folder for later use before replying.

  
  


_ ‘ _ **_If nothing else, it’s taught me the importance of being very, very clear with the stakes in the future, you crazy NTR-loving nympho. I’m not gonna get cheated out of our next bet!’_ **

  
  


**_‘Aww, don’t you want to be my boyfriend? That wasn’t just roleplay you know. You’re incredibly cute. My family is known for being very close with those in their peerages…’_ **

  
  


Had she asked him yesterday, Issei might have literally cut off his left arm for the opportunity. He wasn’t  _ that _ desperate though that he’d be cool with getting cucked for the rest of his life, no matter how hot Rias was.

  
  


And she  _ was _ hot. 

  
  


He hesitated for only a second before shaking his head vigorously to dispel the traitorous thoughts threatening to seep into his mind.

  
  


**_‘I think I’d rather stick my dick in a toaster.’_ **

  
  


**_‘Your dick can fit in a toaster? Oh dear… (＾艸＾)’_ **

  
  


Issei decided then he’d texted enough for the night.


	2. Practise makes Perfect

**Chapter 2: Practise makes Perfect**

  
  


As Issei’s body sagged with exhaustion, he wondered if maybe he had been baited too easily into taking another bet from his King.

  
  


After the smashing success of their previous bet, it didn’t take Rias long to come up with another challenge she hoped her newly minted pawn would also overcome. 

  
  


The challenge? Simple. Just be able to win a spar against Kiba within the week, without the use of his Sacred Gear. Easy, right?

  
  


_ ‘The fuck it is,’ _ Issei thought sourly.

  
  


The challenge was rigged from the start, which Issei should have clued in on given the stakes. And those stakes? If he was able to win, Rias would  _ actually _ let him fuck her, no tricks, none of her ‘NTR’ play. And if he lost? He would be forced to be Akeno’s  _ entertainment _ for an evening.

  
  


Yeah. He probably should have seen the challenge for what it was - payback from Akeno for defeating her in the previous challenge.

  
  


_ ‘I need to stop being blinded by pussy!’ _ Issei raged internally as his eyes flicked over to Rias who watched on, arms crossed under her massive tits with a pleased smile on her devilish features. Beside her stood Akeno, her cheeks tinged pink and almost salivating at his imminent demise.

  
  


It wasn’t like he’d put up a pathetic showing. The  _ only _ reason he couldn’t defeat Kiba was the stupid sacred gear limitation. Kiba’s gear let him create magical swords - pretty cool, but not vital for his fighting style.

  
  


Issei’s gear on the other hand? It was  _ integral  _ to his fighting style. The Boost functionality, he discovered, worked on literally  _ anything _ he did. His body was the first obvious target for Boost’s usage, but then he realized he could narrow the focus for a much greater effect. A single punch, or a simple spell, for instance.

  
  


Issei wasn’t as tragic at magic as the currently salivating sadist seemed to think. He found he was quite adept with telekinesis. One boosted telekinetic crush and this fight would be over, but without boosting the spell, Kiba was easily able to shrug it off.

  
  


Kiba charged at him again. Issei found he was able to follow the much faster knight’s moves, and even match them after promoting to a knight himself, but he just lacked the experience Kiba had with hand-to-hand combat to be of any real threat. He did get a sense of satisfaction when he heard the pretty-boy grunt in pain every time he landed a hit with his higher strength, but Kiba would often counter with a flurry of weaker blows he just couldn’t block.

  
  


It wore his already exhausted body down even more.

  
  


‘That’s time!’ Rias called from the other end of the clearing as Issei finally fell to his knees in exhaustion. ‘You put up a valiant effort, my beloved Pawn, but I’m afraid it’s your loss. The week is up.’

  
  


‘I’m sorry Issei,’ Kiba addressed his new peerage-mate with a sincere apologetic smile. The fact that he looked equally as exhausted was the only thing saving Issei’s pride at that moment.

  
  


Issei shrugged off the apology with a grunt. ‘It’s alright pretty-boy, I got what I needed from our spars.’ 

  
  


‘Ara ara,’ Akeno interrupted their bonding moment with a titter. ‘I believe you have an  _ appointment _ to get to,  _ Is-sei-kun. _ ’

  
  


Issei growled at the ecstatic look on her face, but didn’t argue. He  _ wouldn’t _ be coming out empty handed after this. If this bitch thought she could tame a  _ dragon _ , she was in for a rude awakening.

* * *

  
  


Issei should have been feeling scared and vulnerable in the position he was in, but with Akeno standing before him in a lewd version of her Fallen armour, he just couldn’t find it in himself to care. 

  
  


Her normally impressive black armour with gold trimmings and black feathers was modified in such a way that Issei was finding it hard to take her seriously. Normally, the armour had a black chestplate and armoured skirt that protected her modesty. This ‘lewd version’ had foregone those pieces only for an… armoured micro-bikini? 

  
  


The top strained heroically against her gigantic tits - even more stacked than Rias! - with only two tiny scraps of metal barely covering her nipples. The bottoms were a thong cut so low that he knew she was shaved bare, they also rode high on her hips in a vain attempt to make her look more curvaceous than she actually was.

  
  


‘So what now, chicken legs?’ Issei taunted from his vulnerable position on the floor. She had his wrists bound so they were spread out towards the walls and his ankles bound to hidden manacles on the floor. The end result was him kneeling on the floor, stark naked with arms out wide.

  
  


Issei wasn’t ashamed of his body. His dick was above average in size and his already shredded physique earned from countless hours at the gym became even more so after his devil transformation. He knew there were plenty of girls that would happily want a piece of him, and he was only a virgin still because his standards  _ might  _ be a little too high.

  
  


_ ‘That’s my story and I’m sticking to it.’ _

  
  


‘What was that?’ Akeno asked in a dangerous tone. It seemed he hit a sore spot. Between her and Rias, she may have won in the tits department, but Rias clearly had the more curvaceous body. A rounder butt, thicker thighs, wider hips - you name it.

  
  


Akeno must have known it too.

  
  


‘You heard me. Get on with it, you’ve only got two more hours until midnight.’

  
  


Akeno’s breath quickened and she smiled dangerously at Issei while stroking her riding crop sensuously.

  
  


Without warning, her arm lashed out like lighting and she whipped him across the face with said riding crop. It left a stinging sensation on his cheek, like a light slap, nothing more.

  
  


Issei refused to let any emotion but boredom show on his face as Akeno continued to whip him, the intensity of the strikes increasing as her fury at his non-reaction rose.

  
  


‘Look at you, your pathetic little dicklet is getting hard from this!’ she crowed as she ran her lithe foot up and down his shaft.

  
  


Issei refused to take the bait and shrugged. ‘Once I stopped looking at your little chicken legs and instead focusing on your tits, I couldn’t help myself. They’re really your only redeeming feature.’

  
  


Akeno smiled with her mouth only as she brought her foot back and flicked it forward. Issei groaned as she used the knuckles of her toes to flick his testes with enough force to cause pain to shoot up to his stomach.

  
  


‘How was that,  _ Is-sei-kun? _ ’ Akeno taunted, pleased to finally get a reaction out of him.

  
  


He matched her grin but internally winced at what came out of his mouth next. ‘I’ve got a bit of an itch to the left, you mind scratching it?’

  
  


He thanked whatever higher being was listening that Akeno was clearly not a fan of Bond movies, otherwise he’d look as pathetic as his poor testes felt when Akeno used her riding crop to slap his balls. Hard.

  
  


He couldn’t withhold the scream this time, and he would have curled into a ball if his bound position wasn’t forcing him to stay kneeling as he was.

  
  


‘Oh my, I may have gone a little overboard. Let me help you,’ she said in her caring onee-sama voice as she knelt down, took his balls in her hand and started to send magic into them. Surprised at the sudden surge of warmth in his balls after feeling such pain, Issei was as surprised as Akeno when he groaned and came instantly all over her face.

  
  


Issei laughed openly at Akeno. Her face marred with his cum and her smile frozen on her face.

  
  


‘You are going to regret that, Issei-kun,’ she promised as lightning danced across her fingertips. She slapped him across the face with a lightning-covered palm and Issei convulsed as the electricity surged through his body.

  
  


The fact that he was still laughing at her cum covered face through the pain, in hindsight, was probably not his smartest moment.

  
  


She thunder-slapped him several more times until he was a panting mess at her feet. He didn’t look down though, he stared up at her defiantly - a mocking grin on his lips - as she stood on his erect-again shaft and pressed down on it with increasing pressure.

  
  


‘Is that the best you’ve got, chicken legs? If I’d known you were such an ameteur I’d have volunteered for this sooner. You’re giving sadists everywhere a bad name.’

  
  


Her foot curled around his shaft until her heel was pressed against his tender balls.

  
  


‘If I had known you would enjoy this so much I’d have taken you sooner,  _ little _ masochist-kun.’

  
  


_ ‘It’s ABOVE AVERAGE,’  _ he raged internally, sick of these sluts comparing him with the porn star dongs they seemed to fuck on a daily basis. He let none of this show on his face though.

  
  


‘Let’s make a deal,’ he proposed with a wicked grin. Akeno’s breath hitched in excitement at the thought she might actually get to torture him for more than just that evening.

  
  


‘Oh?’ she asked as she continued to apply pressure to his balls.

  
  


He didn’t let his discomfort show and continued to talk. ‘You have until midnight to make me break and beg for you to stop. If I do, you win. Easy for an  _ expert _ sadist like you, no?’

  
  


Akeno’s breath quickened as the parameters of their latest bet were laid out. ‘The stakes?’ she asked, her pink cheeks growing pinker as she became more aroused. Issei was sure he could even make out her juices leaking out from her little micro thong. He shook thoughts of licking up that trail all the way to its source from his mind and answered.

  
  


‘If you win, I’ll be your toy for a  _ month _ ,’ Issei proposed and Devil damn-it, she nearly came from those words alone. ‘But,’ he interrupted her fantasies with his raised voice. Noticing her attention was back on him he continued. ‘But, if  _ I _ win, you agree to have sex with me, any time I want, for up to  _ six _ months.’

  
  


She looked amused by his proposal.

  
  


‘You want to be my boyfriend, doggy-kun?’ she asked, easing up on the pressure on his balls and circling his shaft with her foot. 

  
  


‘Sex-friend,’ he ammended. ‘As you and Rias won’t even let me forget, I’m a virgin. Who better than a sexy slut like you to practise and get better at sex with?’

  
  


Issei actually found it kinda hot that she didn’t dispute his ‘slut’ slur. ‘And what of my contracts? Do you expect me to stop them during this duration?’

  
  


‘Afraid you’ll lose?’ Issei taunted as Akeno’s smile froze and she put her heel on his balls again and started to apply pressure. His back arched when she pressed harder than before and he gasped out an answer. ‘I don’t care what you do on your time. You’d be a breathing onahole for me during the six months, not my girlfriend!’

  
  


‘Mmm,’ Akeno purred as she eased up the pressure. ‘It’s not like you’ll win and this disgusting little dicklett will come anywhere near me. Deal.’

  
  


Knowing she was now on the clock, she tossed the crop aside and now both of her hands crackled with electricity.

  
  


He wouldn’t break. Despite him teasing her about her chicken legs, Akeno was still arguably even  _ hotter _ than Rias - depending on his mood on the day you asked him. Her onee-sama personality combined with her sluttyness and hidden sadist tendencies was just such a sexy combination, and he’d had fantasies for weeks about playing with those pillowy tits of hers.

  
  


There was  _ no way _ he’d break and lose out on the opportunity of a lifetime.

  
  


Akeno tried. Oh did she try. But when the clock hanging on the wall behind her struck twelve, he looked up with a wide grin - his body still twitching from an over exposure of ‘electrotherapy.’

  
  


With the help of some demonic power and his sacred gear, he was easily able to destroy Akeno’s previously indestructible bindings as he surged to his feet. His grin widened further when Akeno took a step back in shock and a little fear.

  
  


He prowled towards her like a dragon on the hunt. She kept backpedalling until her back hit the wall. Slamming a hand against the wall beside her head in the classic kabedon move he leaned in until his lips were right by her ear.

  
  


‘I win,’ Issei whispered directly into her ear, keeping his voice low so it sounded as deep and husky as possible. He’s practised this move countless times in the mirror in the hopes he’d find himself in this very situation one day. He hoped he didn’t look stupid.

  
  


He was finding it hard to imagine how it  _ wouldn’t _ look stupid. He was still buck naked, his body littered with scars from his ‘playtime’ with Akeno - though they were quickly healing, thanks to his devilish nature - while his dick was as hard as a baseball bat and pointing straight at her. He didn’t even try to avert it, letting it rub against her midsection as he drew closer, his pre-cum leaving a trail against her flushed skin.

  
  


He didn’t care though. And neither did Akeno. Despite her bluster, and all the derogatory comments she made while  _ playing _ with him, she seemed equally as excited and aroused if her elevated breathing and wide eyes were anything to go by.

  
  
  
  


Issei wasn’t fucking around with his wager. He wanted to start collecting as soon as possible, as often as possible. He’d spent a majority of his teen life reading hentai and watching all kinds of porn, but he knew that was a pitiful substitute for the real thing.

  
  


He wanted to be a fantastic lover. Not just  _ average _ like other aspects of his…  _ character _ . To do that he needed practise with the real thing, and who better a teacher than the biggest slut he knew?

  
  


One who is also arguably the most attractive woman he knew.

  
  


It’s how he held on through Akeno’s sadistic ministrations. The thought of this moment, of doing this - of doing  _ her _ \- kept him strong when he otherwise would have given in.

  
  


Akeno moaned and jerked when he sucked her clit into his mouth with as much force as he could manage.

  
  


‘Careful!’ she hissed, grabbing him by the hair and pulling him away from her soaked pussy. ‘Overeager virgins,’ she muttered under her breath before letting out a suffering sigh. ‘Just because the clit is the star of the show, doesn’t mean you go at it full-force until I cum. That’s what virgins who read too much hentai do.’

  
  


Glaring at her, he replied. ‘Then get to teaching, chicken legs.’

  
  


She rolled her eyes. ‘Yes, stimulating the clit feels the best, but just going for broke won’t give the best orgasms. You have to pace yourself. Also, and most important before we continue, every girl is different. What you learn here might not be applicable with the next poor girl you trick into your bed.’

  
  


Issei stopped licking and pulled away from Akeno’s pussy with a frown. ‘Are you really gonna take that tone with me after what I had to go through to get here? If you really don’t want to be here I’ll go. I’m not gonna force you.’

  
  


Akeno rolled her eyes but chose to ignore him. ‘Every girl is different, even if some of the broader strokes are the same. The number one rule for giving great head is learn to read your partner. Pay attention to what they say, sure, but also notice the non-verbal signs - heavy breathing, muscles tensing, back arching, hips bucking etcetera.’

  
  


_ ‘This is gold,’ _ Issei mentally cheered as he nodded at Akeno seriously.

  
  


‘Also, don’t just focus on the clit. Lick the lips and lick around it too. Build anticipation. Make me -  _ her -  _ make her desperate.’

  
  


He positioned himself back between her thighs so she wouldn’t see him smirking at her little slip-up. Akeno had ditched her little metallic thong  _ thing _ but was still wearing the rest of her horny Fallen Angel armour. She lay back on her bed with her legs spread as Issei took instruction.

  
  


He started with slowly running his tongue up one side of her lips, circling but never touching her exposed clit, and then running down the other. He did as Akeno instructed and paid attention to how she reacted to his technique. Her beautiful ass would lift off the bed when he circled her clit and her breathing would increase, and she’d whimper as he drew further away or when he refused to touch the special bundle of nerves.

  
  


Her hand was running through his hair gently as he ate her out, as if showing her gratitude with her actions more than her words. 

  
  


‘Your tongue should never leave my clit or lips,’ she began and squealed when he circled her clit again but chose to plant a chaste kiss on it this time, ‘but that doesn’t mean… that’s all you can do.’

  
  


Issei took immense pride in the fact that Akeno was struggling to instruct as he ate her out. It’s a far cry from the almost bored look and reaction she gave when he started.

  
  


‘Use your fingers too mmm,’ she encouraged. ‘Don’t penetrate my pussy with your tongue, your tongue should keep working my clit and lips, but your fingers can penetrate. Try and find my g-spot. Press against it, stimulate it.’

  
  


_ ‘Now this I think I know!’  _ Issei crowed excitedly as he continued his routine with his tongue, ignoring Akeno’s clit all the while. He backed off so he could insert his index and middle fingers into Akeno’s gushing pussy but didn’t go deep. Instead he curled his fingers back and pressed against the front wall of Akeno’s vagina.

  
  


It was like he had struck her with one of her favourite lightning bolts. Her back arched and she let out a wanton moan at the action. He eased off however, remembering Akeno’s instruction of taking it slow and building up to her orgasm. He continued his tongue routine while also adding pressing on her g-spot to the mix. He timed it so he would brush it gently as he drew closer to her clit with his tongue, and then back off as he eased off.

  
  


Like she taught him, he watched her body’s reactions to his ministrations. Her breathing was steadily increasing, her moans were getting more hurried and wanton and the grip she had on his hair was steadily tightening.

  
  


‘Don’t just sit there all silent, it’s weird,’ Akeno instructed. She was leaning back with her eyes screwed shut in pleasure but she continued to instruct him, in between moans and laboured breathing. ‘Don’t be weird mmmhmm… Giving head is… intimate. Personal. Talk… talk dirty to me. Just talk to me. Tell me you’re enjoying yourself. Tell me you love my pussy.’

  
  


_ ‘Makes sense. It’d be kind of a turn off if a girl was sucking me off and she just looked bored or uninterested with me.’ _

  
  


‘If only your personality was as pretty as your perfect little pussy,’ Issei said the next time he pulled away from her clit. He felt her grip in his hair tightening considerably but he chose to be daring and bit her inner thigh  _ hard _ at her reaction. Her delighted squeal informed him that while not many girls would like that kind of rough treatment, Akeno certainly did.

  
  


‘Look how wet you are down here you cheeky little slut,’ Issei goaded in between his tongue laps of her pussy. ‘I bet you were hoping I’d hold out the entire time.’ 

  
  


He completed another circuit, while steadily increasing the pressure he periodically pressed on her g-spot.

  
  


‘I bet the only reason you shocked me is because you get turned on seeing my muscles tense.’

  
  


He could see and feel it plain as day. Her breathing was coming in quick gasps, her mewls were sounding more desperate and she was almost violently pulling at her own nipples that she’d exposed after tearing off her hilarious micro-bikini top. 

  
  


Then he decided to go in for the kill.

  
  


‘If you’re a good girl, I might even let you do that to me  _ again _ .’ At the final word of his proclamation, he pressed hard into her g-spot and sucked her clit into his mouth with much greater force than she was expecting.

  
  


She squealed but Issei was confused when she leapt up and pushed him away after only barely a microsecond of the intense pleasure. He fell back on his ass and was looking up at the highly aroused looking young-woman in bemusement.

  
  


Akeno allowed her breathing to calm down as she closed her eyes on concentration. Issei took that moment to properly study her heaving tits as she sat crouched on her bed, soaking the sheets with her excretions.

  
  


‘Good… good job,’ Akeno praised when she got her breathing under control. ‘One… one more lesson, and it’s the most important one. Do you want to give your partner the most powerful orgasms imaginable? Every time? Do you want her to black out from pleasure and look at you like you’re a  _ sex god _ ?’

  
  


Issei was nodding along with her questions eagerly as she giggled at his enthusiasm delightfully. It seemed she’d fully gotten on board with the idea of training a lover who would be an expert at satisfying her needy pussy.

  
  


‘Then you need to learn about edging. Do you know what edging is?’

  
  


‘Stopping before you can cum?’

  
  


‘Exactly,’ Akeno nodded with a pleased smile. ‘The more you deny the big O, the more powerful it’ll eventually be. Some girls may not...appreciate it in the moment, but that’s where you need to man up and assert your dominance. She cums when  _ you _ want her to, and when she does, she’ll forget all about the frustration and anger she’s feeling after all the edgings.’

  
  


‘You love it then?’ he asked with a raised brow.

  
  


Akeno closed her eyes and grinned contentedly as she recalled a particularly fond memory.

  
  


‘It makes me squirt every time,’ she admitted with an impish giggle. Issei groaned at the mental image squeezed down on his aching cock that was begging for release.

  
  


‘Let’s take care of that for you while I calm down,’ Akeno offered with her oneesama smile back in place. It looked out of place when she was dressed the way she was, but Issei would have her wearing a garbage bag, he didn’t care.

  
  


They both knew he wouldn’t last long, he’d been hard and horny for  _ hours _ . Still, it came as a shock when she took the entirety of his thick, six and a half inch cock in hour mouth in one smooth motion. Issei groaned in delight and grabbed her pony tail for want of something to do with his hands.

  
  


He could both hear and feel Akeno giggling around his cock and she pulled off until she only had his head in her mouth. She swirled her tongue around his sensitive glands like a seasoned pro - which he supposed she was - before taking the entirety down her throat again.

  
  


Seemingly not satisfied with how long this was taking after half a dozen more throatings like that one, Akeno did something he was  _ never  _ expecting. 

  
  


Issei  _ squealed _ when he felt a foreign invader enter his ass and press on  _ something _ in there. His vision turned white and he saw stars as he experienced the most powerful orgasm of his young life.

  
  


Akeno pulled off him with a giggle as she watched him spasm as stream after stream of hot punk shot out of his overstimulated cock.

  
  


‘Bonus lesson: prostate messages are great,’ Akeno said with an elegant giggle.

  
  


When he finally came to his senses it was to a grinning Akeno standing above him, inspecting some of his cum on her fingers. She locked eyes with him, grinned and stuck her fingers in her mouth before licking them clean in a manner similar to what she’d done with his cock not moments ago.

  
  


_ ‘Akeno is sex-incarnate.’ _

  
  


‘You dick might not be the biggest, but it certainly cums a lot,’ she giggled at his annoyed frown. ‘And you’re an eager learner. Time to see if you pass the final exam.’

  
  


Issei resisted the urge to pin her down and fuck her brains out. He was hard enough, true, but he didn’t want to act the pathetic virgin around her anymore. There’s only so much hits a man’s ego can take.

  
  


He would make her cum harder than she’d just made him cum. The only way he can shut her up about his  _ totally above average and perfectly acceptable  _ dick was to turn her into a gibbering mess the likes of which her donkey-dicked lovers couldn’t even match.

  
  


Akeno’s smile widened at the look of burning determination in his eyes as he slowly pushed her down onto her bed and locked lips with her.

  
  


* * *

He’d been at it for hours. Akeno had lost all sense of cohesion ages ago and he’d had to use her own bindings against her to stop her lashing out at him.

  
  


_ ‘I bet she wasn’t expecting to be edged for this long,’  _ he thought with a self-satisfied mental chuckle. He looked at the clock on the wall and realized it was almost four AM. He didn’t have school tomorrow - today? - so he wasn’t concerned about that, but his eyes were extremely heavy and he was close to passing out himself. His tongue and jaw ached and his cock was sore from the amount of times he’d had Akeno suck him off, or just jacked off on her tits as she lay on her bed, bound with her own magical ropes.

  
  


Issei decided to finally let her cum. He picked up his pace and started to focus more on her clit and g-spot. Her pussy and inner thighs were absolutely  _ soaked  _ and her bedsheets ruined with the amount of juice she’d secreted over the past few hours. 

  
  


Issei had never been more proud in his life. 

  
  


He may have even taken a few pictures and sent them to Rias just in case Akeno tried to lie about the status of their relationship in the future.

  
  


_ ‘Try and make fun of me now with some of the pics I have of you, Akeno,’ Issei thought with a viscous glee. _

  
  


‘Please,’ Akeno begged as she felt her orgasm coming again. ‘Please let me cum. Please, please, please.’

  
  


‘Of course, I think my naughty girl has been punished enough. Daddy will make you feel good.’

  
  


As Akeno started bucking violently in response to his dirty talk, Issei mused again on the little kink he’d stumbled upon with his dirty talk. Akeno must have some wicked kind of daddy issues, because every time he called himself daddy, or told her to call him it, she would  _ lose her mind _ .

  
  


Akeno just continued to plead with him between her moans and quick breaths as he sucked on her clit and rubbed his fingers firmly against her g-spot just the way she loved it.

  
  


‘Yes, yes, yes, yes, yes, yeeeeeeeeeeees,’ Akeno squealed when he finally allowed her to cum.

  
  


_ ‘Holy shit look at her go!’  _ Issei marvelled as he hips bucked and she squirted a fountain of juice from her pussy. He’d seen guys drinking the squirt in porn but Issei wasn’t entirely convinced it wasn’t just diluted piss yet.

  
  


Akeno would just have to be content with the uber powerful orgasm she was receiving. He continued to gently rub her clit as her hips bucked with her climax while also leaning down and feasting on her pillowy tits with delight. Her nipples were smaller than Rias’, but her tits were bigger and flopped around on her chest as she moaned and convulsed in pure ecstasy.

  
  


Issei felt pretty pleased with himself when Akeno just fell asleep after she was done cumming, sheer exhaustion likely knocking her out as much as the power of her orgasm.

  
  


_ ‘Either way, I’m taking it.’ _

  
  


It was way too late to go home so he decided to curl up next to Akeno, pull the covers over them both and catch some shut-eye himself. He could feel exhaustion’s effect on him too and after pulling Akeno into his broad, muscled chest - taking one of her magnificent tits in hand too, of course - he passed out almost as soon as his head hit the pillow.


End file.
